Water → HCID 11100743, compound

HRID 1245832Notes

Reaction equation

HRID 1245832 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][OH:7].C(N(CC)CC)C.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20].O>ClCCl>[S:19]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)([O:7][CH2:6][CH2:5][O:4][C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[Br:1])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 111068022-(2-bromophenoxy)ethanol

Product 1

HCID 11100743HCID 11100743, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Bromophenoxy)ethanol (17.4 g) was dissolved in dichloromethane (250 ml) and cooled to 0° C. Triethylamine (9.7 g) was added along with tosyl chloride (18.3 g). The mixture was stirred for 2 h, then added to water (500 ml). The organics were washed twice with 2N hydrochloric acid and dried. Separation was achieved using silica chromatography eluting with hexane/ethyl acetate mixtures. This gave 2-(2-bromophenoxy)ethyl tosylate (14.4 g).

Workup

  1. washThe organics were washed twice with 2N hydrochloric acid
  2. customdried
  3. customSeparation
  4. washeluting with hexane/ethyl acetate mixtures

Sources & evidence

ORD record
ord-52de1dbe91884cec8503d719a6be67f6
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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